Water → 5-Bromo-2-(propoxymethyl)-1-benzofuran

In THF (57 ml) was dissolved 5-bromo-2-(hydroxymethyl)-1-benzofuran (5.7 g), and to the solution was added at 0° C. 60% sodium hydride (1.4 g). The mixture was stirred at room temperature for 1 hour, and to the mixture was added at 0° C. 1-bromopropane (3.1 ml). The mixture was stirred at 65° C. for 16 hours and cooled to room temperature. The reaction solution was poured into water, and the mixture was extracted with ethyl acetate, washed with saturated brine and dried with magnesium sulfate. Under reduced pressure, the solvent was removed, and the residue was purified with silica gel column chromatography (hexane/ethyl acetate=8/1) to give 5-bromo-2-(propoxymethyl)-1-benzofuran (5.0 g).

1. additionto the solution was added at 0° C
2. additionto the mixture was added at 0° C
3. stirringThe mixture was stirred at 65° C. for 16 hours
4. temperaturecooled to room temperature
5. extractionthe mixture was extracted with ethyl acetate
6. washwashed with saturated brine
7. dry with materialdried with magnesium sulfate
8. customUnder reduced pressure, the solvent was removed
9. customthe residue was purified with silica gel column chromatography (hexane/ethyl acetate=8/1)

ORD record

ord-97fdec39cb0049898a3a4a1d840a0c86

Source dataset

uspto-grants-2001_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06235771B1